4-(1-Methylpiperidin-4-yl)aniline → N-Methyl-N-(3-{2-[4-(1-methyl-piperidin-4-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzyl)-methanesulfonamide

HRID 472464Notes

Reaction equation

HRID 472464 reaction equation
Cl[C:2]1[N:23]=[C:5]2[C:6]([C:10]3[CH:11]=[C:12]([CH:20]=[CH:21][CH:22]=3)[CH2:13][N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:24][N:25]1[CH2:30][CH2:29][CH:28]([C:31]2[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[CH3:19][N:14]([CH2:13][C:12]1[CH:20]=[CH:21][CH:22]=[C:10]([C:6]2[C:5]3[N:4]([N:3]=[C:2]([NH:37][C:34]4[CH:35]=[CH:36][C:31]([CH:28]5[CH2:27][CH2:26][N:25]([CH3:24])[CH2:30][CH2:29]5)=[CH:32][CH:33]=4)[N:23]=3)[CH:9]=[CH:8][CH:7]=2)[CH:11]=1)[S:15]([CH3:18])(=[O:17])=[O:16]

Participants

4

Reactant 3

HCID 219595294-(1-Methylpiperidin-4-yl)anilineHCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 67479008N-[3-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-benzyl]-N-methyl-methanesulfonamide

Product 1

HCID 59612511N-Methyl-N-(3-{2-[4-(1-methyl-piperidin-4-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzyl)-methanesulfonamide

Procedure

N-Methyl-N-(3-{2-[4-(1-methyl-piperidin-4-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyridin-8-yl}-benzyl)-methanesulfonamide was prepared from N-[3-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-yl)-benzyl]-N-methyl-methanesulfonamide (75.0 mg, 0.214 mmol) and 4-(1-methyl-piperidin-4-yl)-phenylamine (45.0 mg, 0.236 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (24.0 mg, 0.0439 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.039 g, 36%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.43 (d, J=6.5 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 7.96 (s, 1H), 7.59 (d, J=7.1 Hz, 1H), 7.55-7.50 (m, 3H), 7.42 (d, J=7.5 Hz, 1H), 7.21 (d, J=8.3 Hz, 2H), 6.96 (t, J=7.0 Hz, 1H), 6.81 (s, 1H), 4.42 (s, 2H), 3.01-2.94 (m, 2H), 2.87 (s, 3H), 2.83 (s, 3H), 2.50-2.40 (m, 1H), 2.33 (s, 3H), 2.09-2.00 (m, 2H), 1.87-1.73 (m, 4H). MS=505 (MH)+.

Sources & evidence

ORD record
ord-c9d52d0e332244189f95b769e0900583
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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